The Devil himself visits Jim to remind him of the deal they made years ago, when Jim promised to give away his fifth child if the Devil helped him win over Cheryl.

Jim looks forward to a "guys only" weekend with Andy, but when Andy ends up dumped by Emily over a text message and when the guys stumble upon Emily's depressed ex husband, Jim decides to do his best to cheer up the guys and save what's left of their weekend.

While out for dinner and a movie, Jim loses a parking spot, and later loses Cheryl when he can't let go of it.

Jim actually remembers his and Cheryl's anniversary - but Cheryl didn't! Improvising, she gives him the photo album that covers years worth of memories. They start reminiscing.

Cheryl and Jim have an evening at home without the kids and decide to stay in and just have dessert for dinner. But Jim's choice of pastries causes a spat which morphs into an all-out food fight. The next day they laugh off the night's argument; Jim is thrilled that they don't seem to have to talk things out. But then Andy, who's out for revenge on Jim for coaxing his kids to play pranks on him, counsels Cheryl to really dissect and analyze her marital arguments.

Jim is horrified when he sees his son Kyle with a green Packers ball. He tries by all means to change it for a Bears one, but the kid just can't let go of the green ball. Jim has nightmares about it and takes Kyle to his work in another attempt to get rid of the Packers ball. When he realizes there's nothing he can do about it, he does a little alteration on the ball so they can go to the Bears game peacefully.

Jim takes umbrage at being replaced as the father in a promotional shoot for a cruise line.

Cheryl's mother, Maggie, wants Jim, Cheryl and the family to rest someday in a family plot she reserved years ago, but Jim insists on his own family plot--then secretly reserves a a plot for himself next to a star football player.

When Cheryl returns home for a visit the kids end up occupying her time, so Jim decides to prepare a special date with her at the airport lounge, only to end up mistakenly arrested.

Jim is forced organize a doll-themed party for Gracie while Cheryl is on bed rest, but when Gracie admits that the only reason she agreed to the party was because she wanted to please her mother, Jim decides to turn the party into something totally else.

Jim urges Andy to propose to Emily or risk losing her, but when he sees Emily dining with another man, he doubts the wisdom of his advice.

Dana's first task at the ad agency is to cast the perfect TV family for a Disney cruise commercial. Cheryl and the kids get the job, but Dana's boss replaces Jim with a handsome actor in the role of "dad."

Cheryl believes she's attending a tasteful lingerie party, but is shocked to learn the hostess is selling sex toys and Cheryl buys one, but won't tell Jim.

Jim and his band win a chance to play for a child pop sensation Jami McFame, but when the star gives them an attitude, Jim decides to set her straight.

When Cheryl learns of Jim's plan to use their twins in a movie starring Steve Guttenberg to get some money for Christmas gifts, she refuses to let him do it, but Andy and Jim decide to go through with the plan anyway, only to have it backfire when the producers cut the kids hair to make them look alike.

Jim's bad back has him on prescription pain pills which has him in an altered state and opens up an opportunity for the family to share information which usually would upset him.

Cheryl's 15 year-old cat Mr. Feeney dies and she wants Jim to bury it on the backyard, but Jim desperately wants to go to the Bears game. He sticks the cat in the garage freezer, planning on burying it after the game, but Cheryl finds out before he comes home. She is hurt that Jim doesn't listen to her nor care about a cat that has been longer with her than anything in her current life. Jim, feeling guilty, provides a proper funeral for Mr. Feeney and gets her a brand new dog, which she doesn't like very much at first, but starts to accept it later.

Jim and Cheryl agree to let Ruby model for a print ad as a one-time thing, but when the photographer calls her a natural, Jim gets Ruby an agent.

After Jim is diagnosed with high blood pressure, Cheryl decides to do everything to help him. She makes him special food, give him backrubs, and keeps asking about his day in order to free him from stress. But Jim doesn't know how to share so much and tells her an old financial problem of the firm. Cheryl stays up all night doing math to figure out a way out of the problem. Jim says she has a disease and is always trying to help people, which Cheryl responds with stop caring about him. In the end, they finally settle their issues when Jim says he loves her and would be a total mess without her.

It's Kyle and Andy's birthday, and Andy is feeling a little left out of his own special day. They decide to take him to a restaurant that serves a 4,5 lbs steak, and Jim offers to pay for the check because Cheryl isn't feeling equal to Dana, who's spending a lot of money on their kids. On the table, Dana says she doesn't mind paying the check because she makes more money than Jim, which enfuriates him. He buys a donkey for the girls so they can know he's the one they should go to if they want stuff (in this case, they wanted a poney, but "they'll never know the difference"), and it isn't until the donkey ruins a painting Dana bought for Kyle's room that they talk it out and settle their issues.

On a family trip to Vegas, Cheryl secretly plans a reunion with Jim and his estranged sister, Roxanne, on the special, one-hour season finale.

Cheryl tries to impress her boastful cousin Mindy by posing as the lead singer of Jim's band – even though she has a terrible voice. Jim agrees to perform at Mindy's engagement party with Cheryl playing the part in order to teach his wife a lesson about embellishment by making a fool of herself. However, when Mindy tells Jim that her fiancé, Eric, is a record producer, he must decide between telling Cheryl the truth and making a bad impression on Eric.

Cheryl ask Jim to use his truck to transport a giant paper-mâché grizzly bear the girls made for "spirit week" to their school – except Jim just lost his truck in an arm wrestling match and, in a gesture of macho pride, refuses to ask for it back.

The fifth season premieres with Jim sneaking off to a Cubs game with Kyle instead of taking him to his first day of kindergarten.

When a proud and happy Ryan announces that Dana is pregnant, Jim warns him of Dana's upcoming hormone swings, and ends up dreaming that he is pregnant.